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Chatterbox

Yelp Rating - 3.7 stars(104)Yelp logo
(914) 495-3900
user provided Chatterbox photo
CategoriesBars, New American, Italian
Location75 Cooley St, Pleasantville, NY
user provided Chatterbox photo

Gift Tips

  • Save a gift card for a weekend dinner and try the lobster ravioli or spaghetti carbonara — both are frequently mentioned as standout pasta choices.
  • Order shareable plates like grilled calamari, bacon-wrapped shrimp, or mussels so a group can sample several items from the menu.
  • Plan for outdoor seating in pleasant weather to enjoy sunset views — the patio is noted as a lovely spot for a relaxed evening.
  • Try the Blood Orange Spicy Margarita at the bar for a notable cocktail choice.
  • If bringing a group, consider arriving earlier on busy nights or mention a reservation detail clearly — the staff is helpful getting parties seated and accommodating.

Click here to send a gift up to $1,000 with the suggestion to use it at Chatterbox.

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Hours
Monday-Saturday: 11AM-10PMSunday: 11AM-9PM
Chatterbox map location

Chatterbox is a restaurant and bar located in Pleasantville, NY. It sits in a neighborhood that blends suburban comfort with an upbeat dining scene, making it a popular choice for dinners, gatherings, and casual nights out.

  • Ambiance: A lively, modern dining room with outdoor seating that offers sunset views and a warm neighborhood vibe in Pleasantville.
  • Cuisine: New American with strong Italian influences, featuring large portions, pasta specialties, seafood, and a full cocktail and bar program.
  • Highlights: Generous portions, friendly service, creative cocktails (try the Blood Orange Spicy Margarita), and a mix of quiet and festive nights including karaoke and events.

The menu mixes Italian classics with New American touches, offering items from pizza and pasta to seafood and shareable starters. Many dishes come in sizable portions, so it’s a good spot for families or groups who like to take leftovers home. Staff members are noted for being friendly and attentive, and a few servers are regularly praised for their service.

Chatterbox is a versatile option for different occasions: a lively Saturday night for those who want an energetic atmosphere, a sunny outdoor meal to enjoy the view, or a weekday lunch for a relaxed bite. The bar area and themed nights add to the restaurant’s social appeal without sacrificing food quality.


Customer Reviews
Dean H.
Yelp Rating - 5 stars01/07/2026
Great food and service! Friendly wait staff. Nothing like getting your own iPad menu. lol. My first but fun. Great apps! read review
Greg R.
Yelp Rating - 1 stars01/28/2026
Disappointed by the food. Disappointed by the service. I will no longer return. Feels like I threw my money is a trash can. read review
Tia M.
Yelp Rating - 5 stars01/04/2026
What a great place!! The ambiance is beautiful, the staff is amazing and the food is top notch!! Took the girls there for lunch on Christmas break and it... read review

Great Alternatives

Gift $100 for Dolphin South Trattoria: Indulge in an exquisite culinary journey at Dolphin South Trattoria in Pleasantville, where impeccable Italian cuisine and a warm, inviting ambiance come together to create an unforgettable dining experience.

Buy a Gift & Greeting Card for La Riviera: Step into a world of elegance and charm at The Riviera in Pleasantville, a delightful destination offering exquisite cuisine and a captivating ambiance.

Updated: February 13, 2026

The Giftly Advantage

With Giftly you strike a perfect balance, the thoughtfulness of a Chatterbox gift card with the flexibility of money.

  • Easy to buy online. Have it delivered now or later
  • Send it with a personalized greeting card
  • 3 easy ways for your recipient to redeem the gift
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How it works

  1. You customize a gift
    Gift up to $1,000 with the suggestion to use it at Chatterbox. Delivered in a personalized greeting card.
  2. They receive the gift
    Gifts can be sent by email, SMS*, mail or you can print it yourself.
  3. They enjoy it!
    They redeem the gift on our website and choose to deposit the funds in their bank account, Paypal account or to have a Visa / Mastercard Gift Card mailed to them.
They can spend the money at Chatterbox or anywhere else they like!

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